This invention relates to m-dioxane-5-methylamines and their pharmaceutically acceptable acid-addition salts having analgesic activity as well as the 2-substituted-1,3-propanediols which are useful intermediates in the preparation of such compounds.
In equianalgesic doses, morphine and its synthetic surrogates produce approximately the same incidence and degree of unwanted side effects. Nevertheless, there are some patients who may have side effects with one agent and not with another; therefore the surrogates are useful additions to the therapeutic regimen. When the pain is likely to be of short duration (e.g. diagnostic procedures, cystoscopy, orthopedic manipulations, etc.) a drug with a shorter duration of action might be preferable to morphine or methadone.
It is a purpose of this invention to provide m-dioxane-5-methylamines and their pharmaceutically-acceptable salts having analgesic activity. Many of the instant compounds have analgesic activity of short duration with minimal untoward side effects such as tolerance or physical dependence.
Several compounds containing a 1,3-dioxolane nucleus in their chemical structure are reported to have analgesic activity. Dexoxadrol, d-2,2-diphenyl-4-(2-piperdyl)-1,3-dioxolane hydrochloride, is a mild analgesic with a high incidence of psychotomimetic side effects [Lasagna and Pearson, Proc. Soc. Exp. Biol. N.Y. 118, 352 (1965)]. N,N,2-Trimethyl-1,3-dioxolane-4-methylamine is a mild analgesic with cholinergic side effects [McClure, Arch. int. Pharmacodyn. 179, 154 (1969)].